Sailing Classes & Lessons in the Hamptons 

Most people think you have to grow up around boats to learn to sail. You don’t. At our sailing school in the Hamptons, complete beginners step aboard, take the tiller, and pick up the basics the same day. Sag Harbor Sailing is a family-run, ASA-accredited school. We’ve been teaching here since 1997, and we’ve graduated hundreds of ASA-certified sailors, from kids to retirees. Lessons run in small groups on calm, protected water. Our instructors have spent decades on these bays. Whether you want a single lesson or full ASA certification, this is where you start.

Our School and Our Approach

We’re an ASA-accredited sailing school. That means our courses follow the standards of the American Sailing Association, and the certifications you earn are recognized across the country. But accreditation is only part of it. What students remember is the teaching.

Our instructors are licensed by the U.S. Coast Guard, and most have 20 or more years on the water. They teach in plain language, not jargon. They keep groups small, so everyone gets real time at the helm. Lessons happen on our 23-foot Pearson Ensigns. These are classic keelboats, stable and forgiving, which makes them a good boat to learn on. On a first lesson, you’ll learn the parts of the boat, how to read the wind, and how to steer and trim the sails. By the end, most students have taken the helm and sailed a few legs on their own.

We keep things calm, literally. Most lessons stay in the protected back bays around Sag Harbor. The wind is steady and the water is gentle. That’s a far easier place to learn than open, choppy ocean.

Your Lesson Options

We teach sailors at every level, from first-timers to people ready to skipper on their own. Here’s how the options break down.

Group Lessons

Group lessons are our most popular way to start. You learn alongside a few other students in a relaxed, social setting. Group lessons run up to three sessions a day through the summer season, which runs from mid-May through the end of September.

Private Lessons

Private lessons are for one-on-one attention at a pace that’s all yours. Our private sailing lessons take up to four students per session, so the coaching stays focused.

Beginner Cruising

ASA certification makes it official. Our two-day ASA beginner certification course (ASA 101) teaches you to handle a 23-foot keelboat in light to moderate wind. The certification is recognized nationwide and good for life.

Intermediate Cruising

Intermediate cruising is for sailors who already have the basics. We offer intermediate keelboat cruising instruction to build your skills and your confidence.

Youth Summer Camp

Youth summer camp is for younger sailors. Our youth summer program gets kids ages 9 to 16 out on the water all summer.

Not sure where to begin? Call or text us, and we’ll point you to the right starting point.

Who Learns With Us

Our students are all kinds of people. Some have never touched a tiller. Others sailed years ago and want to shake off the rust. A few are working toward a charter trip or buying their own boat.

We teach ages 8 to 80 and up. Kids pick it up fast, and we’ve taught plenty of adults who always meant to learn and finally did. You don’t need any experience to start a beginner lesson. You don’t need to own gear or a boat. You just show up ready to learn.

If you’re nervous about it, that’s normal. A lot of first-timers are. Our instructors are used to teaching people who’ve never been on a sailboat, and the calm bay water makes those first lessons a lot less intimidating. Once you’ve got the basics down, many of our students go on to rent a sailboat and head out on their own.

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Why Learn With Us

Plenty of places in the Hamptons will take you out on a boat. Fewer will actually teach you to sail one. We’re a dedicated sailing school, not a charter company that offers a lesson on the side.

That focus shows up in a few ways. We’re ASA-accredited, with an award-winning sailing education program. We’ve graduated hundreds of ASA-certified sailors since 1997. Our instructors are USCG-licensed and bring 20-plus years on the water. We keep groups small, so you learn by doing, not by watching.

Sailing is a skill you keep for life. We’d rather you leave knowing how to read the wind and handle the boat than just having had a nice afternoon. Both can be true, but the skill is the point.

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Sailing School in the Hamptons

We’re based at the Yacht Hampton Boating Center at 51 Pine Neck Avenue in Sag Harbor, on the East End of Long Island. Lessons sail out from there into the protected bays nearby.

These back bays are part of why Sag Harbor is such a good place to learn. The water is calmer than the open ocean. There’s plenty of room to practice without crowds of powerboats. You’ll get views of Shelter Island and the North Haven shoreline while you work on your tacks and jibes.

Sag Harbor itself is an easy, scenic place to spend a morning or afternoon, with the village and harbor right there when you come off the water. We welcome students from across the Hamptons and the East End, whether you live here year-round or you’re out for the summer.

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Lessons & Classes

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Private Sailing Lessons

Location Sag Harbor
$475 + Fuel, Staff & Gratuity
Length 23
Capacity 4
Crew 1 Captain
Bathroom(s) 1
Trip Type Day
More Info
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American Sailing Association Certification Course Image 1
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American Sailing Association Certification Course

Location Sag Harbor
$990 + Fuel, Staff & Gratuity
Length 23
Capacity 4
Crew 1 Captain
Bathroom(s) 1
Trip Type Day
More Info

All boats will be captained by a USCG licensed captain.

Hours & Pricing

Morning Session, 9:00 am–12:00 pm: $1,500 per week or $500 per day

Sessions runs from Monday, July 1 through August 30, 2024

$40 gratuity for counselors & crew are included in registration checkout.

 

FAQs

NEED AN ESCAPE?

Lets have a fun and memorable day!

Ready to Learn to Sail?

You don’t need experience, your own boat, or a free week. You just need a willingness to get out on the water. Pick a group lesson, a private session, or a full ASA course, and we’ll handle the rest. Call or text us at (631) 725-5100 with a question, or to book your first lesson. We’d love to teach you to sail.